Bifunctional compounds having a norbornane skeleton are known to show excellent characteristics when used as adhesives and resin raw materials. Tricyclodecanedimethanol and pentacyclopentadecanedimethanol are known as bifunctional compounds having a norbornane skeleton, and some production methods are reported (see, for example, Patent Document 1).
Patent Document 2 discloses a method for producing tricyclodecanedimethanol by subjecting dicyclopentadiene to a hydroformylation reaction to form dialdehyde and hydrogenating the dialdehyde.
Patent Document 3 discloses a method for producing tricyclodecanedimethanol or pentacyclopentadecanedimethanol by hydroformylating dicyclopentadiene or tricyclopentadiene using a rhodium compound as a catalyst, adding an extraction solvent composed of a polyalcohol to the resulting reaction solution to separate the rhodium complex catalyst into the hydrocarbon-based reaction solvent layer and the reaction-product tricyclodecanedicarbaldehyde or pentacyclopentadecanedicarbaldehyde into the extraction solvent layer, and subjecting the extraction solvent layer to hydrogen reduction in the presence of a hydrogenation catalyst.
Tricyclodecanedimethanol described in Patent Documents 2 and 3 is a compound in which one norbornane and cyclopentane mutually share a plurality of atoms to form the main skeleton as shown in the following formula (A). Pentacyclopentadecanedimethanol described in Patent Document 3 is a compound in which two norbornanes and cyclopentane mutually share a plurality of atoms to form the main skeleton as shown in formula (B) or formula (C).
